Butyl isocyanate → HCID 22235541, compound

HRID 1743736Notes

Reaction equation

HRID 1743736 reaction equation
[C:1]([C:3]1[CH:29]=[CH:28][C:6]([O:7][CH2:8][CH2:9][CH:10]([NH:20]C(=O)OC(C)(C)C)[CH2:11][N:12]2[CH:17]3[CH2:18][CH2:19][CH:13]2[CH2:14][NH:15][CH2:16]3)=[CH:5][CH:4]=1)#[N:2].C(N(CC)CC)C.[CH2:37]([N:41]=[C:42]=[O:43])[CH2:38][CH2:39][CH3:40]>CC#N>[NH2:20][CH:10]([CH2:9][CH2:8][O:7][C:6]1[CH:28]=[CH:29][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[CH2:11][N:12]1[CH:13]2[CH2:19][CH2:18][CH:17]1[CH2:16][N:15]([C:42]([NH:41][CH2:37][CH2:38][CH2:39][CH3:40])=[O:43])[CH2:14]2

Participants

5

Reactant 3

HCID 8110Butyl isocyanateHCID 8471TriethylamineHCID 22235347HCID 22235347, compound

Product 1

HCID 22235541HCID 22235541, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-Butyl 3-(4-cyanophenoxy)-1-(3,8-diazabicyclo[3.2.1]oct-8-ylmethyl)propylcarbamate (100.1 mg, 0.25 mmol; see Preparation M) was dissolved in MeCN (2.5 mL) and triethylamine (37.9 mg, 0.38 mmol). Butylisocyanate (29.7 mg, 0.3 mmol) was added and the reaction mixture was stirred at r.t for 4 days. The solvent was evaporated and the resulting residue dissolved in ethyl acetate (0.5 mL). Ethyl acetate saturated with HCl (2 mL) was added and the mixture was stirred for 6 h. The solvent was evaporated and the residue dissolved in MeCN (2 mL). The solution was added to ion-exchange solid phase extraction plug. The plug was then eluted with DCM/MeCN (4×2 mL of 4:1) (fraction 1) followed by DCM:MeOH:Et3N (4×2 mL of 8:1:1)(fraction 2). Evaporation of fraction 2 gave the title compound in quantitative yield.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe resulting residue dissolved in ethyl acetate (0.5 mL)
  3. additionEthyl acetate saturated with HCl (2 mL) was added
  4. stirringthe mixture was stirred for 6 h
  5. customThe solvent was evaporated
  6. dissolutionthe residue dissolved in MeCN (2 mL)
  7. additionThe solution was added to ion-exchange solid phase extraction plug
  8. washThe plug was then eluted with DCM/MeCN (4×2 mL of 4:1) (fraction 1)
  9. customEvaporation of fraction 2

Sources & evidence

ORD record
ord-32079aaff856444181fbb9493d5c29ac
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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